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Organophotocatalytic carbo-heterofunctionalization of unactivated olefins with pendant nucleophiles. | LitMetric

Organophotocatalytic carbo-heterofunctionalization of unactivated olefins with pendant nucleophiles.

Chem Sci

Laboratory of Organic Chemistry, Department of Chemistry and Applied Biosciences, ETH Zürich 8093 Zurich Switzerland

Published: July 2023

AI Article Synopsis

Article Abstract

We report the difunctionalization of unactivated, terminal olefins through intermolecular addition of α-bromoketones, -esters, and -nitriles followed by formation of 4- to 6-membered heterocycles with pendant nucleophiles. The reaction can be conducted with alcohols, acids, and sulfonamides as nucleophiles furnishing products bearing 1,4 functional group relationships that offer various handles for further manipulation. Salient features of the transformations are the use of 0.5 mol% of a benzothiazinoquinoxaline organophotoredox catalyst and their robustness with respect to air and moisture. Mechanistic investigations are carried out and a catalytic cycle for the reaction is proposed.

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Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC10321488PMC
http://dx.doi.org/10.1039/d3sc02250aDOI Listing

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